Think Chicago Bulls and you immediately think of Michael Jordan and Scottie Pippen.

The two legends were at the heart of the Bulls' near decade-long period of dominance in the 1990s, combining to propel the franchise to six championships in eight years.

But as good as they were on the court together, it turns out Pippen's basketball smarts didn't exactly translate to the real world.

Speaking on Zach Lowe's ESPN podcast, Amin Elhassan said Jordan would scam Pippen out of $100 every game day, and Pippen had no idea he was being hustled.


Cartoon races featuring three bulls would be played on the jumbotron at Chicago Stadium during a time-out and Jordan would bet Pippen $100 he could pick the winner. What Pippen didn't know was that Jordan had reportedly come into the stadium early one day and was told by the operations crew all the races were pre-recorded and they knew who would win before it went up on the screen.

Being the GOAT, Jordan was fed the information about which character would win and that day he collected a cool $100 from his good friend after correctly picking the winner. He didn't just stop there though, but allegedly continued to add a Benjamin to his bank balance every game for an entire season after making the same bet over and over.

What's most remarkable if the story is true is that Pippen never figured out the secret behind MJ's winning formula, so every couple of days he'd part with some hard earned green (though for an NBA star $100 is hardly a noteworthy sum), no doubt blaming it on bad luck and thinking he would have a chance to recoup his losses next time around.

How wrong he was.

Jordan's gambling was the stuff of legend, at times seen gambling in casinos in the early hours the day of important games in playoff series and even the 1992 Barcelona Olympics. There was also a conspiracy that his first retirement from basketball in 1993 was actually a suspension brought on by his penchant for gambling.